Koenigs-Knorr Synthesis of Cycloalkyl Glycosides

Abstract

Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorrsynthesis of 2-(4-methoxybenzyl)cyclohexyl-β-D-glycopyranosides. Using this promotermodel glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols weresynthesized in 50–60 % overall yields. Diastereoisomeric mixtures of products wereobtained in these syntheses, which started from racemic isomers of 2-(4-methoxy-benzyl)cyclohexanol. The prepared compounds have been purified and characterized bytheir 1H- and 13C-NMR spectra, as well as by their IR and MS spectra, in order to usethem as reference compounds in planned subsequent research.

Keywords

• Koenigs-Knorr synthesis
• Cycloalkyl-β-D-glucopyranosides
• Cycloalkyl-β- D-galactopyranosides
• Cadmium carbonate.